2,6-Di-tert-butyl-4-methylphenol → (1S,2S)-2-(4-{(R)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-5-trifluoromethyl-indan-1-yloxy}-phenyl)-cyclopropanecarboxylic acid ethyl ester

HRID 471461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471461
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20](Br)[C:21]([C:25]([F:28])([F:27])[F:26])=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2].[C:30]([Si:34]([CH3:46])([CH3:45])[O:35][C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1)([CH3:33])([CH3:32])[CH3:31].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O1CCOCC1.O.[Cl-].[NH4+].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([C:39]4[CH:40]=[CH:41][C:36]([O:35][Si:34]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:45])[CH3:46])=[CH:37][CH:38]=4)[C:21]([C:25]([F:28])([F:27])[F:26])=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2]

Komponenten

9

Edukt 4

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 75806TricyclohexylphosphineHCID 111078154-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 86703893(1S,2S)-2-[4-((R)-4-Bromo-5-trifluoromethyl-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester

Produkt 1

HCID 86703892(1S,2S)-2-(4-{(R)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-5-trifluoromethyl-indan-1-yloxy}-phenyl)-cyclopropanecarboxylic acid ethyl esterAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 25517Ammonium ChlorideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

(1S,2S)-2-[4-((R)-4-Bromo-5-trifluoromethyl-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester (200 mg, 0.43 mmol), 4-(tertbutyldimethylsilyloxy)phenylboronic acid (118 mg, 0.47 mmol) potassium carbonate (176 mg, 1.28 mmol), 2,6-di-tert-butyl-4-methylphenol (47 mg, 0.21 mmol), tricyclohexylphosphine (10 mg, 0.03 mmol), and Pd2(dba)3 (16 mg, 0.02 mmol) are suspended in a mixture of dioxane (1.7 mL) and water (0.6 mL) in a sealed tube and heated at 110° C. for 4 hours. The mixture is diluted with saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried and concentrated under vacuum. The residue is purified by flash chromatography (eluent: 0-30% EtOAc in cyclohexane) to give the title compound (Yield 90 mg)

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is dried
  3. concentrationconcentrated under vacuum
  4. customThe residue is purified by flash chromatography (eluent: 0-30% EtOAc in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-5729f19259d845fea7812d12de707552
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633182B2

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